KR950014182A - Method for producing biodegradable polyimide or polypeptide hydrolyzate thereof - Google Patents

Method for producing biodegradable polyimide or polypeptide hydrolyzate thereof Download PDF

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KR950014182A
KR950014182A KR1019940031070A KR19940031070A KR950014182A KR 950014182 A KR950014182 A KR 950014182A KR 1019940031070 A KR1019940031070 A KR 1019940031070A KR 19940031070 A KR19940031070 A KR 19940031070A KR 950014182 A KR950014182 A KR 950014182A
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acid
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salts
amino
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베르나르 쟝-마리
르빠제 쟝-뤼뜨
뽕스 아르노
뚜르니라끄 플로렝스
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마들레느 프랑스 파브로
롱-쁠랑 쉬미
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    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
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    • C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
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    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
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Abstract

Process for the preparation of polyimides or of their polypeptide hydrolysates with a biodegradability of at least 80%, by thermal polycondensation of at least one amino acid and then, optionally, hydrolysis, the thermal polycondensation stage being carried out in the presence of at least one "acid catalyst" chosen from . sulphuric, nitric, phosphorous, sulphurous, hydrofluoric, silicic and sulfonic acids, organic sulfonic acids containing less than 50 carbon atoms, amino acids carrying a strong acid functional group which is not a carboxylic acid functional group, organic phosphonic acids and organic carboxylic acids having a pKa less than or equal to 5 and preferably less than or equal to 3; . precursors of these acids; . salts of these acids and of an amino acid which is the same as or different from that or those used; . salts of these acids and of a polyimide derived from the polycondensation of at least one amino acid which is the same as or different from that or those used; . hydrochloric acid and its precursors; . salts of hydrochloric acid and of an amino acid which is the same as or different from that or those used, when the amino acid to be polycondensed is other than glutamic acid; . salts of hydrochloric acid and of a polyimide derived from the polycondensation of at least one amino acid which is the same as or different from that or those used; . acid salts of sulphuric, phosphoric or phosphorous acids or their precursors; . precursors of phosphoric acid other than phosphorus pentoxide or polyphosphoric acids; . and Lewis acids; according to an "acid catalyst"/amino acid molar ratio of at least 0.001. Use of the polyimides or of the polypeptide hydrolysates thus obtained in detergent compositions, and detergent compositions containing the said polyimides or hydrolysates.

Description

생분해성 폴리이미드 또는 그의 폴리펩티드 가수분해물의 제조방법Method for producing biodegradable polyimide or polypeptide hydrolyzate thereof

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (13)

황산, 질산, 인산, 아황산, 불화수소산, 규산 및 술폰산, 탄소수 50미만, 바람직하게는 탄소수 25미만의 유기 술폰산, 비카르복실계 강산 작용기를 갖는 아미노산, 유기 포스폰산, pKa가 5 이하인 유기 카르복실산; 상기 산의 전구물질; 상기 산의 염, 및 사용된 아미노산과 유사하거나 상이한 아미노산의 염; 상기 산의 염, 및 사용된 아미노산과 유사하거나 상이한 1종이상의 아미노산의 중축합으로부터 유도된 폴리이미드의 염; 염산 및 그의 전구물질, 중축합되는 아미노산이 글루탐산 이외의 산일 경우, 염산염, 및 사용된 아미노산과 유사하거나 상이한 아미노산의 염; 염산염, 및 사용된 아미노산과 유사하거나 상이한 1종이상의 아미노산의 중축합으로부터 유도된 폴리이미드의 염, 황산, 인산 또는 아인산의 산성염 또는 그의 전구물질; 무수 인산 또는 폴리인산 이외의 인산 전구물질; 및 루이스산으로부터 선택된 1종이사의 "산촉매"의 존재하에 "산촉매"/아미노산 몰비를 0.001 이상으로 하여 열 중축합 공정을 수행함을 특징으로 하는, 1종이상의 아미노산을 중축합시킨후 임의로 가수분해함으로써 생분해도가 80%이상인, 폴리이미드 또는 그의 폴리텝티드 가수분해물을 제조하는 방법.Sulfuric acid, nitric acid, phosphoric acid, sulfurous acid, hydrofluoric acid, silicic acid and sulfonic acid, organic sulfonic acid having less than 50 carbon atoms, preferably less than 25 carbon atoms, amino acids having non-carboxylic strong acid functional groups, organic phosphonic acids, organic carboxyl having pKa of 5 or less mountain; Precursors of the acids; Salts of these acids, and salts of amino acids similar or different from the amino acids used; Salts of the acids, and salts of polyimides derived from polycondensation of one or more amino acids similar or different from the amino acids used; Hydrochloric acid and its precursors, when the polycondensed amino acid is an acid other than glutamic acid, hydrochloride, and salts of amino acids similar or different from the amino acids used; Hydrochloride, and salts of polyimides derived from polycondensation of one or more amino acids similar or different from the amino acids used, acid salts of sulfuric acid, phosphoric acid or phosphorous acid or precursors thereof; Phosphoric acid precursors other than phosphoric anhydride or polyphosphoric acid; And a thermal polycondensation step of carrying out a thermal polycondensation step with a "acid catalyst" / amino acid molar ratio of at least 0.001 in the presence of one or more "acid catalysts" selected from Lewis acids. A method of producing a polyimide or a polypeptide hydrolyzate thereof having a degree of 80% or more. 제1항에 있어서, "산촉매"가, 메탄술폰산, 벤젠술폰산, 트리플루오로메탄술폰산, 도데실벤젠술폰산, p-톨루엔술폰산 또는 시스테인산, 무수 또는 수화 황산, 발연 황산, 칼륨, 리튬, 나트륨 또는 4차 암모늄의 산성황산염, SO3,, 황산 암모늄, 산/중성염 몰부기 0.5∼1∼10/1인 중성 알칼리 금속 황산염/황산, 또는 중성 알칼리 금속 또는 알칼리 토금속 황산염/인산 또는 피로인산 혼합물, 칼륨, 나트륨, 리튬 또는 4차 암모늄의 인산 수소염, HCI, PCl3, POCl3, 시아누르산 클로라이드, SiCl4, CH3SiCl3,살리실산, 클로로아세트산 등, 포스포메틸글리신, 에틸포스폰산, 아스파르트산 히드로클로라이드, 아스파르트산염 및 황산, 메탈술폰산 및 p-톨루엔술폰산의 염, 폴리안히드로아스파르트산 히드로클로라이드, 또는 AlCll3, BF3, ZnC12임을 특징으로 하는 제조방법.The method of claim 1, wherein the “acid catalyst” is methanesulfonic acid, benzenesulfonic acid, trifluoromethanesulfonic acid, dodecylbenzenesulfonic acid, p-toluenesulfonic acid or cysteinic acid, anhydrous or hydrous sulfuric acid, fuming sulfuric acid, potassium, lithium, sodium or Acidic sulfates of quaternary ammonium, SO 3 , ammonium sulfate, neutral alkali metal sulfates / sulfuric acids with an acid / neutral molar moiety of 0.5-1 to 10/1, or neutral alkali metal or alkaline earth metal sulfates / phosphates or pyrophosphate mixtures, Hydrogen phosphate salts of potassium, sodium, lithium or quaternary ammonium, HCI, PCl 3 , POCl 3 , cyanuric chloride, SiCl 4 , CH 3 SiCl 3, salicylic acid, chloroacetic acid and the like, phosphomethylglycine, ethylphosphonic acid, Aspartic acid hydrochloride, aspartate and salts of sulfuric acid, metalsulfonic acid and p-toluenesulfonic acid, polyanhydroaspartic acid hydrochloride, or AlCll 3 , BF 3 , ZnC1 2 . . 제1항 또는 제2항에 있어서, 사용된 아미노산이, 아스파르트산 또는 글루탐산 단독, 또는 소정 비율로 함께 혼합되거나 다른 아미노산과 혼합된 형태의 아스파르트산 또는 글루탐산임을 특징으로 하는 제조방법.The method according to claim 1 or 2, wherein the used amino acid is aspartic acid or glutamic acid alone, or aspartic acid or glutamic acid in a form mixed together or mixed with other amino acids in a predetermined ratio. 제1항 또는 제2항에 있어서, 열 중축합 공정이 100℃∼250℃의 온도에서 수행됨을 특징으로 하는 제조방법.The process according to claim 1 or 2, wherein the thermal polycondensation process is performed at a temperature of 100 ° C to 250 ° C. 제1항 또는 제2항에 있어서, 열 중축합 공정이 벌크 또는 용매 매질내에서 수행됨을 특징으로 하는 제조방법.The process according to claim 1 or 2, characterized in that the thermal polycondensation process is carried out in a bulk or solvent medium. 제1항 또는 제2항에 있어서, 아미노산/"산촉매"혼합물 대신에 반응의 단독 구성성분으로서 "아미노산염"을 사용함을 특징으로 하는 제조방법.The process according to claim 1 or 2, wherein "amino acid salt" is used as the sole component of the reaction instead of the amino acid / "acid catalyst" mixture. 제1항 또는 제2항에 있어서, 중축합 공정이, 중축합 전체 공정을 통해 미분쇄 또는 취화 형태로 존재하며 "산촉매"가 균일하게 분배된 반응 매질을 이용하여 벌크로 수행됨을 특징으로 하는 제조방법.The process according to claim 1 or 2, characterized in that the polycondensation process is carried out in bulk using a reaction medium in which the "acid catalyst" is present in the finely divided or embrittled form throughout the entire polycondensation process and the "acid catalyst" is uniformly distributed. Way. 제7항에 있어서, -물(또는 그외의 휘발성 액체 희석제)을 이용하여 아미노산 및 고형 또는 액체 "산촉매"의 혼합물의 페이스트를 생성하고, 진공 또는 대기압하에서의 증발에 의해 물(또는 희석제)을 제거한 다음, 수득된 물질을 분쇄하거나; -아미노산 및 고형 또는 액체 "산촉매"를 물(또는 그외의 아미노산 및 촉매 용해제)에 용해시킨 다음, 용액을 미립화하거나; -고형 또는 액체 "산촉매"용액중 아미노산이 물(또는 그외의 촉매 용해제)중 현탁액을 미립화시키거나, -고형 또는 액체 "산촉매"의 수용액(또는 그외의 촉매 용해제중 용액)을 아미노산의 유동성 배드 상에서 증발시키거나; -아미노산 및 고형 "산촉매"의 혼합물을 공분쇄 또는 미립화시킴으로써 "산촉매"가 반응 매질내에 균일하게 분배됨을 특징으로 하는 제조방법.8. The method of claim 7, wherein water (or other volatile liquid diluent) is used to produce a paste of a mixture of amino acids and a solid or liquid “acid catalyst”, and the water (or diluent) is removed by evaporation under vacuum or atmospheric pressure. Pulverizing the obtained material; -Dissolve the amino acid and the solid or liquid "acid catalyst" in water (or other amino acids and catalyst solubilizers), and then atomize the solution; The amino acid in the solid or liquid "acid catalyst" solution atomizes the suspension in water (or other catalyst solubilizer), or-an aqueous solution of the solid or liquid "acid catalyst" (or solution in the other catalyst solubilizer) on the fluidized bed of amino acid Evaporate; A process wherein the "acid catalyst" is uniformly distributed in the reaction medium by co-pulverizing or atomizing the mixture of the amino acid and the solid "acid catalyst". 제7항에 있어서, "산촉매"/아미노산 몰비가, "산촉매"가 산성염 또는 산성염 전구물질로 구성될 경우 0.001∼0.15이고, "산촉매"가 산성염 또는 산성염 전구물질 이외의 화합물일 경우 0.001∼0.005임을 특징으로 하는 제조방법.8. The molar ratio of "acid catalyst" / amino acid according to claim 7, wherein the "acid catalyst" is 0.001 to 0.15 when the "acid catalyst" is composed of an acid salt or an acid salt precursor, and is 0.001 to 0.005 when the "acid catalyst" is a compound other than an acid salt or an acid salt precursor. Characterized in the manufacturing method. 제1항 또는 제2항에 있어서, 염기성 제제를 첨가함으로써, 열축합에 의해 수득된 폴리이미드를 폴리펩티드염으로 가수분해하고, 임의로, 무기 또는 유기산을 첨가함으로써 상기 염이 이후에 폴리펩티드산으로 중화됨을 특징으로 하는 제조방법.3. The method according to claim 1, wherein by adding a basic agent, the polyimide obtained by thermal condensation is hydrolyzed into a polypeptide salt and optionally, by adding an inorganic or organic acid, the salt is subsequently neutralized with the polypeptide acid. Characterized in the manufacturing method. 세제 조성물용의, 제1항 내지 제10항중 어느 한항의 방법에 따라 수득된 폴리이미드 또는 그의 폴리펩티드 가수분해물.A polyimide or a polypeptide hydrolyzate thereof obtained according to the method of any one of claims 1 to 10 for a detergent composition. 전하 밀도 COO-가 0∼5×10-4몰/중합체 1g의 범위일 수 있고 세제욕내에 10-3몰/중합체 1g 이상의 전하 밀도 COO-를 부여할 수 있으며, 제1항 내지 제10항중 어느 한항의 방법에 따라 수득된 폴리이미드 또는 그의 폴리펩티드 가수분해물을 함유하는 세제 조성물.The charge density COO − may range from 0 to 5 × 10 −4 mol / polymer 1 g and impart a charge density COO − of at least 10 −3 mol / polymer 1 g in the detergent bath, wherein any one of claims 1 to 10 A detergent composition containing a polyimide or a polypeptide hydrolyzate thereof obtained according to the method of claim 1. 제12항에 있어서, 폴리이미드 또는 그의 폴리펩티드 가수분해물이 세제 조성물 중량의 0.2∼80%임을 특징으로 하는 세제 조성물.13. The detergent composition of claim 12, wherein the polyimide or polypeptide hydrolyzate thereof is 0.2-80% of the weight of the detergent composition. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019940031070A 1993-11-24 1994-11-24 Process for preparing polyimides or their biodegradable polypeptide hydrolysates KR100201264B1 (en)

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FR9314042A FR2712892B1 (en) 1993-11-24 1993-11-24 Process for the preparation of polyimides or their biodegradable hydrolysates.
FR9314043A FR2712896B1 (en) 1993-11-24 1993-11-24 Detergent composition containing a biodegradable polyimide or a hydrolyzate of said polyimide.
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